


Problems

by AmethystWinchester



Category: Supernatural
Genre: Angst, Angst with a Happy Ending, Anxiety, Dean Winchester Actually Deals With Feelings, Epilogue, F/F, F/M, Fix-It, Happy Ending, Heaven, Hell, Human Castiel (Supernatural), M/M, Post-Finale
Language: English
Status: In-Progress
Published: 2020-12-22
Updated: 2021-01-07
Packaged: 2021-03-10 18:39:53
Rating: General Audiences
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 3
Words: 6,862
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/28161798
Author URL: https://archiveofourown.org/users/AmethystWinchester/pseuds/AmethystWinchester
Summary: Time is weird. It’s always been hard to follow. It passes faster in heaven but slower in hell.After Dean’s Death, life goes on. Sam starts a new life with a family of his own. Dean is finally in heaven... unless he’s not. When he gets in the impala to drive off, things start getting weird. He needs to escape but what is he escaping from? When does Sam find out about this? Is it too late?But what even is too late? Time is just an illusion. Anyways, that is something we can think about later, we’re starting somewhere else.
Relationships: Benny Lafitte/Dean Winchester, Castiel/Dean Winchester, Charlie Bradbury/Rowena MacLeod, Eileen Leahy/Sam Winchester
Comments: 1
Kudos: 6





	1. Chapter 1

* * *

“Wake up, Castiel.” His bright blue eyes opened immediately. He had been begging for them to open for so long. Well... he didn’t know how long it had been. Time barely made sense anymore.

“Jack?” He said as he looked at the kid. More like someone who used to be a kid. Jack was supposed to be about three years old. He’s never looked or acted his age. Still, this time something was different.

”You- you have his power now, don’t you?” Castiel asked reluctantly. He was starting to have a hard time seeing extra power as a good thing. 

  
“Yes, I do.” Jack said calmly. 

Cas sensed a new kind of maturity in him. “So you actually pulled me out of there? This is real?”

“Yes, I did, and it is.” He smiled. 

  
The Empty was obviously a horrible place. It truly messed him up. Every second was filled with constant regret, and Cas had a lot to regret. He tried not to think about it. He couldn’t cry or freeze up in front of anyone, but he was feeling so weak. Even when he stopped thinking he couldn’t stop feeling. He felt sad. He felt scared. He felt... hungry?

”Jack, what did you do?” 

“I took your grace. This way you’re human and the Empty can’t take you back.” 

Castiel didn’t respond. He didn’t know what to think about this. He felt like he should be sad... but he wasn’t. Not really. This could be his chance to just live out his life and to grow old with Sam and-

Dean. He was thinking about so much that he didn’t have a chance to think about Dean. Now he would be all he could think about. How could he even go back to him now? Before he was killed he confessed his love for him. He couldn’t imagine Dean forgetting about that. 

“Jack, how long has it been? Where are-”

“I know you have a lot of questions, but I can’t answer them all right now.” Jack interrupted. “Dean isn’t where he’s supposed to be and I need time to fix that.” He snapped his fingers and disappeared. 

“Jack, wait!” He looked up and realized he was somewhere new. He stood in front of a nice little house in a neighborhood full of similar houses. He wasn’t sure what else to do but to see who lived in this house. Jack had to have brought him here for a reason. 

He slowly walked up to the door. He hesitated before ringing the doorbell. He stepped back as he heard footsteps and waited as the door opened. 

A very tall man opened the door. A very familiar tall man. 

“Cas?” He sounded surprised and slightly doubtful. 

“Yes, Sam, it’s me.” 

Sam smiled brightly and then hugged him. “How are you back? It’s been a year! Wow, am I glad to see you”

Cas flinched at the hug. “What? It’s been a year?”

Sam stepped back. “Well yeah, it’s been over a year now since everything happened, I didn’t think you were coming back after everything I saw.”

Cas was confused. “What do you mean everything you saw? Where is Dean?” 

Sam’s smile faded. “Uh... why don’t you come inside.”

Cas followed him inside. He was very surprised to see Eileen walking towards the door. 

“Sam-” She stopped as she saw them. “Castiel?” 

Sam nodded. She signed something to him and she signed back. She looked at Cas and smiled “I’m glad you’re back. I’ll let you two talk.” She started to leave. 

Cas looked down at her stomach. “Wait, are you two... having a child?” He asked, sounding surprised. 

She nodded and smiled. “His name is Dean.”

“Oh really? How does Dean feel about that?” Cas asked.

Eileen looked at Sam. _He doesn’t know?_ She signed.

Sam shook his head.

Cas squinted slightly. “It seems like I really have missed a lot.” He said as he looked at Sam. 

“Yeah, uh... we’re actually married now.” He smiled. “But Cas I really need to tell you something. Maybe you should sit down.”

Eileen looked at Cas, frowned, and left the room.

Cas tilted his head to the side. “Okay?” He sat down on Sam’s couch. “First, tell me what you meant by everything you saw.”

Sam looked down. “Well I don’t want you to be mad but- okay... Dean wouldn’t tell me anything about what happened and I just needed to know why and if there was a way to get you back. Long story short I looked at the security footage and I saw everything.”

Cas looked embarrassed “You saw everything I said? I’m sure Dean couldn’t have been pleased with that.”

Sam sighed. “I just need to tell you this right now. Dean died about a year ago.” He was finally getting used to just saying it. The thought of Dean in Heaven was becoming more comforting than sad.

“What?!” Cas stood up immediately. “No- no he couldn’t have-”

His thoughts started spiraling. All he wanted was for Dean to live a full, normal life. He sacrificed himself thinking Dean would live on. He thought since he was back he could grow old with Dean, even if he’d have to push his feelings away. This was not supposed to happen. 

“We need to get him back! Why have you waited a year?!”

”Whoa, calm down. I know how you feel about Dean and I know you want him back but that’s not what he wants. He’s in heaven now! He can finally be at peace, Cas!”

Heaven. Of course he’d be in heaven but-

He remembered what Jack had told him. 

“Dean isn’t where he’s supposed to be.” Cas said flatly. 

“What?” Sam sounded confused. 

“Dean isn’t where he’s supposed to be!” He shouted. “That’s what Jack told me. Dean has been in hell for a year and no one has done anything about it!” His voice broke. He was so angry.

“Are you sure?” Sam started sounding very worried.

”Yes, I’m sure!” 

“Well we have to do something about it now then!” Sam started feeling guilty for not trying to get him back.

”Jack says he needs to fix it.” Cas sighed. 

“Oh yeah? Where was he for the past year?!” Sam yelled. 

Cas knew he was right. “So we’ll have to do this ourselves.”

”Okay so can you just zap us down there now to go get him?” Sam asked. 

“I’m afraid it’ll be a bit more complicated than that.”   
  


* * *

  
Dean started driving away. He had such a weird feeling that he tried to ignore. What Bobby said just didn’t sit right with him. Cas was out of the Empty fixing Heaven and he wasn’t there to say hi? 

He figured Cas must’ve been too busy. He knew he’d see him again eventually. Things started getting weird as he kept driving.

It started getting dark. Extremely dark. At first the sun started setting as if the day was ending. That was weird to begin with but he didn’t really know how time worked in this new heaven yet. 

Then all of the sudden everything was pitch black.

He was about to slam on the breaks as the headlights went out. Before that could happen he heard a crash.

The headlights went back on. The sky went from pitch black back to a nice sunset. Dean quickly looked around. Did he just imagine all of that? 

He stepped out of the car to see if he’d hit something. His mouth dropped wide open. It wasn’t something, but someone.

”Benny?” Dean asked with surprise and disbelief.

“Dean?” Benny asked as he sat up and groaned. “Did you just hit me with your car?”

“Yeah well I uh... sorry about that- but what the hell, man? How’d you get here?” Dean asked, still not entirely believing it.

”I have no idea, where is here?” He asked.

”Heaven! We’re in Heaven!” His look of shock faded into a smile. “Never thought I’d see you here.”

”Well I’ve gotta be honest, it’s a surprise to me that you’re here too!” He chuckled.

”Benny, how did this happen? I mean not that I’m complaining but you in Heaven?”

”I can’t explain it but I can’t say it’s the worst thing that’s ever happened to me.” He shrugged.

”So you just appeared here? When it happened I think Heaven kind of broke for a minute.”

”Well, leave it to me to break Heaven.” He laughed.

”This must’ve been Jack or- or Cas...” Dean started trying to figure it out. Jack would probably be able to figure out anything he wanted to, right? He surely knew how important Benny was to him and brought them together. What if it was Cas? He’d just want Dean happy, but after everything he said... well if he knew how close Dean and Benny were, he probably wouldn’t have done this.

”Don’t think too hard about it, Dean. Let’s just enjoy it.” Benny put his arm around Dean and smiled.

Something didn’t feel right about this. Dean wasn’t sure if it was because it seemed too good to be true, or if it had something to do with Cas. After Cas’ confession Dean wanted to tell him so much. He just didn’t have time. He was absolutely shocked at everything that was said.

Dean thought that Cas would be waiting for him in Heaven. He planned on telling him how he really felt. If Cas would show up with Benny around, things would be much more complicated.

”So what now?” Benny asked.

”Well, I think we can do anything we want to here! I’ve just been driving around, I’m not really sure how everything works yet-”

”Okay then.” Benny interrupted. “Let’s just keep driving.”

They both got in the car and back on the road. Dean started getting confused as he drove ahead.

”It looks like we’re back where we started... I mean it’s as if I turned around completely and drove the whole way back, but I don’t think I’ve been driving in a circle.” He kept driving down that road until he saw something that made him quickly pull the car over.

”What is it?” Benny asked.

”My old house...” Dean started to wonder if that was where his parents lived. He opened the car door and stepped out. “Come on.” He said to Benny as he walked towards the house to knock on the door.

No one answered. “Hello?” He yelled. When there was was still no answer, he tried to open the door. To his surprise, it was unlocked. He opened it and walked inside. “Is anyone home?” He asked as he walked in. He turned around as he realized Benny didn’t follow him.

”Hey, Benny, are you coming?” He stopped talking when he saw someone coming around the back of the house. He started walking back towards Benny to see who it was but he had disappeared from sight.

”What is it, Dean? Did you see someone?” Benny looked around.

Dean’s eyes widened as Benny turned his head. “No, stop!”

Before either of them knew what was happening a machete slashed through the air and Benny was on the ground.

“NO!” Dean yelled as he ran towards him. “Benny, please no!” His eyes started to water. He slowly looked up at the man who did it. His eyes filled with rage.

”Dad-” His voice broke. “How- how could you?!”   
  


* * *

“Great, Dean is in hell and you’re powerless.” Sam kicked a chair.

”Well that’s not going to help-”

Sam cut Cas off. “I don’t care! Dean’s been in hell for a year and I’ve done nothing!”

Cas glared at him. “I’m upset too. You have no idea how upset I am! I’m sorry you feel bad about this but now we actually can do something so stop complaining about it and help me think of something!”

“Like what?! Everyone who could help is probably dead!” Sam yelled.

”Jack isn’t dead!”

”Well he clearly doesn’t seem set on helping!” Sam responded angrily.

”At least we could try! Why wouldn’t he anyway? We will find him again and he will help!” Cas yelled.

”If you’re so sure about that, why don’t you go find him?!”

”Fine, I will.” Cas stormed out of the house.

He made sure he was out of sight. “Jack? Can you hear me?” He called.

Jack appeared in front of him. “Castiel, I told you I’m busy.”

”Busy doing what?!” Cas asked. “You should be doing something about Dean!”

”I’m working on it.”

”That isn’t good enough!” Cas said angrily. “You should’ve been working on it a year ago! It should’ve taken you a few seconds!”

”It isn’t that easy. He’s been to Hell and so his soul should be stuck there. He somehow managed to get stuck between Heaven and Hell instead and he’s going to have to get himself through.” Jack told him.

”That doesn’t make any sense! You have the power of God, you must be able to get him out of there!” Cas yelled.

”I’m sorry.” Jack said sadly before disappearing again.

Cas went back into the house. “Sam, something is really wrong.”

Sam looked at him like he was crazy. “Obviously something is wrong, Dean is in Hell!”

”No, not that.” He rolled his eyes at him. “Jack isn’t making any sense. He told me he’s stuck between Heaven and Hell and that he has to get himself out.”

”What? Jack is like the new God, he should be able to do anything!” Sam sounded confused.

”Exactly, there’s something he’s not telling us.” Cas said slowly as he thought about it.

”Like what?” Sam asked.

”How would I know?” Cas responded.

”Okay then, I’m going to do some research.” Sam walked off.

Cas sighed and kept thinking about what could be going on.

* * *

”Why would you do that?! How did that happen? He’s dead, he’s still dead! People aren’t supposed to die in Heaven! Why is he not coming back?!” Dean just kept yelling to avoid crying.

”Dean, calm down right now.” John Winchester said firmly.

”You just killed my- you killed Benny! Don’t ask me to calm down!” He shouted.

”Don’t talk to your father like that.” He said sternly.

”I’m sorry-” Dean started to respond quietly. “Well, no. Actually I’m not at all sorry! You killed- you killed my friend! This is Heaven, it’s supposed to be perfect! There’s not supposed to be killing here!”

”If he was here, he was already dead. I hopefully sent him back where he belongs.”

”You mean purgatory? He didn’t belong there, he didn’t do anything wrong!” Dean was so angry.

”Yes, he did! That’s a monster, Dean, a monster. We get rid of monsters. You failed at it while you were alive and that’s bad enough, but you can’t even kill a dead vamp?! I expected more from you.”

”I- what do you mean I failed at it while I was alive?! I saved the world so many times!”

”Yet you made friends with things like Benny.”

”That’s it.” Dean said as he walked away. He got back into his car and started driving. Once he got far enough away his eyes started watering again.

“Damn it Jack, what’s happening?! This isn’t supposed to happen here!” He slammed his hand on the steering wheel and turned the music up so loud that he couldn’t hear himself think.

After a few minutes he turned the music off and pulled over again. He took a minute to think about what he was going to say.

“Hey, uh... Cas? I really don’t know if you can hear me but-” He took a deep breath. “What am I saying? I know you can hear me so you better listen up. Cas, you told me you loved me and then you left me. I didn’t even have time to think! You left me you dumb son of a bitch! You know what? I still need you. So you better come back to me right now!” He got louder and louder as he spoke.

”And guess what? Your little new and improved Heaven? Not very Heavenly! I don’t know if it was you who brought Benny here but now he’s dead because of my dad. Everything sucks right now and that’s not what’s supposed to happen. This is so stupid, could you please just come here so we can talk?!”

He looked around and sighed when Cas didn’t show up. “Thanks a lot, Cas.”


	2. Burning Pile

Sam turned around as there was a loud knock on the door.

“Are you expecting someone?” Castiel asked.

”No...” He walked up to the large wooden door and peaked through the window beside it. His tired and upset expression turned to one of fear and confusion.

”Who is it? What’s wrong?” Cas asked.

”It’s not her. It can’t be.” Sam stepped away.

”Who?” The blue eyed man was becoming impatient.

He didn’t answer. The frightened man pulled out an angel blade which he stashed in his pocket after Cas returned and swung open the door.

“Why are you not dead?!” He yelled.

”Calm down, Sam. Aren’t you glad to see me again?” The brunette woman smirked.

Cas took a few steps closer to the door so he could see if the familiar voice belonged to who he thought it did. “Ruby?”

She looked at him and smiled.

“Hello, Castiel.” Her gaze moved back to the man she’d tricked into helping her to raise Lucifer from Hell.

”Oh, Sam... it’s been way too long. You know, I’ve really missed you! It’s just too bad you had to kill me.” The demon frowned.

He rolled his eyes and tried not to look flustered. “It was mostly Dean who killed you. He’s dead now and you should be too so how the hell are you here?!”

Ruby chuckled. “You’re always so serious. Your angel buddy here got me out.”

Castiel tilted his head to the side. “I did?”

”Aww don’t try to hide it from Sam, you promised you’d get me out, and now I’m here!” She looked at Sam with another smirk, clearly enjoying his frustration.

”You stay right there.” Sam quickly slammed the door shut and walked away.

”Sam, she’s lying. I didn’t get her out.” Cas looked annoyed.

”I really don’t care.” He opened a cabinet to grab a can of spray paint. “We need to get a demon trap under the rug so we can hold her here. We’re going to use her to get to Hell. Now go out there and keep her distracted.”

Cas sighed and went outside. “Hello again, Ruby. I apologize about Sam, he’s just slightly concerned.”

”Of course he’s concerned. It’s alright. You know, I haven’t come here to cause trouble. I mean, why would I do something to hurt the person who helped me out of that horrible place?” She smiled.

The door opened once again. “You two should come inside.” Sam said flatly.

”Well thank you for the offer but I’m fine here.” Ruby crossed her arms.

”Come inside.” He said sternly.

”Well okay, if you insist.” She glared at him before following Castiel inside. After taking a few steps she couldn’t go any further. “Damn it! I trusted you.”

Sam chuckled. “Yeah? I trusted you too. Now listen up. Dean is in Hell and you’re going to get him out.”

She laughed. “Aww that’s so cute, you really think I’ll help? The moment you release me I’m gone.”

”Well then we’re not releasing you.” Castiel said as he started coming up with a plan. “We’re going to make a deal, you’re going to send my soul to Hell, and I’m going to go get Dean back.”

“Perfect.” She smiled. 

Sam wanted to object but he felt desperate. “I’m going too.”

Ruby laughed. “Sorry, but that’s not part of the deal. Besides, don’t you want to stay here to make sure I’m not a bad girl?” She made a pouty face.

“Fine!”

“Good.” The seemingly brown eyed demon smirked yet again. “Are you ready for Hell, Castiel?”

“Yes.” As soon as the word left his mouth, his body hit the floor, and his soul was transported somewhere else.

* * *

Dean got out of his car and started walking down an unfamiliar path. After a few minutes he decided to turn back. It was too quiet and that meant his thoughts could be loud.

As he walked back towards his car he noticed a second path. He looked up and saw a woman walking down the path. She walked slowly as if she wasn’t sure where to go from there.

As Dean got closer he realized she looked familiar. Her wavy red hair gave it away.

“Charlie?!” He called out as he moved faster.

She turned around. “Dean?! Oh my gosh, you’re here!” She quickly ran to him and launched into a hug.

He pulled her in tightly. “Hey- hey I’m so glad to see you here.” He said softly.

“Why are you here?! Don’t tell me you’re dead already-“ she frowned.

“Well... yeah. It’s okay though, Heaven is better than what I was left with on earth.”

Honestly, not much was taken from him. Almost everyone he loved was back. He could’ve done anything he wanted to, but Cas was gone. He was gone, and that was enough. 

“Heaven? So we are in Heaven?” She looked happy but surprised.

“What do you mean?” Dean sounded confused. “Haven’t you been here for a while?”

“No, uh... give me a second.” She ran up the path and looked around a corner.

“Hey, wait- Charlie?” He called after her. “What are you doing?”

“Hey, Ro?” She yelled.

“Yes?!” A voice that was instantly recognized by Dean answered immediately.

“We made it! Now come on!”

“Ah, look who we have here.” Another red haired woman said with a smile after turning the corner.

“Rowena?!” Dean was even more confused. “How the hell did you work your way up from- well... Hell?”

“It’s a very long story.” Charlie sighed.

“I think we kind of have all the time in the world, so tell me.” He crossed his arms.

“Well, okay. Charlie and I have been together-“

“Like... together, together?” Dean asked jokingly.

“No!” Charlie said almost too quickly.

The witch tilted her head to the side as she looked at her. “We sure we’re five minutes ago when we were-“

“Whoa, whoa, I was joking-“ Dean didn’t mean to start this discussion. “But... you and her-“

“I don’t wanna talk about it!” Charlie crossed her arms.

Rowena looked offended. “Fine then. Well, she was in Hell, I was the queen of Hell. I didn’t want the poor girl getting tortured any longer and she’s had her experience as a queen-”

“Don’t make fun of me.” Charlie interrupted.

“I wasn’t.” Rowena said with a chuckle. “So anyways, I let her rule by my side. We got to tell everyone what to do and everyone respected us for a long time.”

“You ruled Hell at each other’s sides? Sounds like you two are pretty serious.” Dean raised an eyebrow.

Charlie crossed her arms. “Maybe.” She muttered quietly.

“After a while, people started to... make it known that they didn’t appreciate our leadership.” Rowena sighed.

“Yeah, and then we pretty much had to run for our lives.” Charlie rolled her eyes. “But luckily Ro knew about how Heaven is kinda under construction, and we found a way to break through!”

“Okay hold up, you just broke through Hell to Heaven? That means just anyone could do it, right? That sounds bad.” The exhausted man said with a sigh. “So we’ve gotta take care of it now that you’re here, we’ve gotta seal them apart again.”

“We’re not just anyone, but I’m sure you’re right.” Rowena smiled. “We should get started.” 

They started walking back where the girls came from.

Dean paused as he started to notice the things happening around them.

“You’re both seeing this right?”

The sky was getting weirdly dark in random areas. It’s like what happened when- he didn’t want to think about it. Dean couldn’t get his hopes up for Benny to appear again.

No one answered him. He was starting to realize how weird this was.

“I uh... I think I’m just going to go back to my car to do some research on this first.”

Charlie grabbed his arm. “Oh come on, we need to stick together! Besides, Rowena knows everything we need to know.”

“Fine. Let’s go.”

* * *

Castiel let out an anguished scream as he opened his eyes.

The man who used to be an angel wasn’t used to feeling like this. He was not prepared for the agonizing pain.

Castiel really didn’t have time to think about this. He obviously knew it wouldn’t be pleasant in Hell as a human, but this was worse than he’d imagined. His arms and legs were chained. He felt like being pulled apart. It was getting harder to think. He needed to stay focused. Finding Dean was all that mattered.

“Hello?!” His voice broke as he yelled. “Hello?!” He kept calling out but no one answered.

“Dean? Sam? Ruby?!” There was still no answer. He was alone. All alone.

The only thing he could think about was how Dean could’ve been going through this for a year. A year on earth, which would feel like over a hundred years in Hell.

“Dean!” He yelled. “Please hear me! I’m sorry- I’m so sorry. I wasn’t there, I couldn’t get you back, but I’m here now!”

He didn’t want to give up but all hope was slipping away.

“DEAN!”

* * *

“Come here, Sam. Don’t keep yourself so far away.” Ruby frowned. “It’s been so long since we’ve seen each other and you couldn’t even give me a kiss to say hello?”

Sam glared at her. “Did you actually think this would be a happy reunion? Do you know how much trouble you caused for me? I hate you! Now leave me alone.”

“Leave you alone? I’m the one trapped here! Don’t you remember all the fun we used to have? We can be like that again if you just let me out of here.” She crossed her arms.

“No way. You’re insane. By the way, I’m married now so don’t get any ideas.” He scoffed.

“Married? You? I never thought that would happen.” She laughed.

“Shut up. You’re not going to talk your way out of this so just sit there and be quiet.”

She kept laughing. “You really think you have any control over this right now? You don’t even know what’s happening to Castiel! Oh just wait until you find out everything I know! I’m winning Sam! You can’t win unless you join me!” This was way too familiar to Sam.

He could remember everything from that awful night like it just happened. He remembered her shouting about her victory and how how it was all because of him.

He refused to let it happen again.

“No! You don’t know anything. This is what you do, you lie and you- you manipulate! Castiel is going to get Dean. We don’t need any help from you besides what you can do from sitting right there.” He turned away.

“Castiel isn’t going anywhere!” She laughed.

“What? You made a deal, he’s going to get Dean and then you’ll bring him back.” He glared at her.

“We agreed that I’d send him to Hell to get Dean, but I never said I’d bring him back. He’ll never get to Dean anyway! You might as well stick his body on the burning pile like you did with all of your other friends. They’re all gone.”

“You’ll bring him back or I’ll kill you!” He yelled.

“If you kill me, who’ll bring him back? Also, he’s not really the one who brought me back, did you know that? It was an old friend of yours. The most powerful being in all of creation and he’s on my side!”

“Jack would never be on your side.”

“Oh Sammy, it’s not Jack.”


	3. Baby Boy

* * *

“What the hell do you mean?” Sam took a cautious step closer to Ruby.

“Why the hell should I tell you?” She glanced up at him.

“Again, I can just kill you if you don’t.” He held up his angel blade.

“And again, you need me.” She reminded him.

“Listen, I will never need you for anything at all, ever again. There are a ton of other demons who’ll be more helpful than you.” He took another step, pointing the angel blade at the demon.

“And there are plenty more people who I could be helping but here we are baby boy.” Ruby said while trying to seem completely unbothered.

Sam shot her a glare. “Never call me that or anything like it again.”

“Why not?” She asked with a smug expression across her face. “Weren’t you just a baby boy when you and your mommy started kissing up to demons? It doesn’t seem like anything has changed. Well, other than the fact that you still look down on us but now you expect help without consequence.”

“You sent my friend to Hell, sorry that I’m kind of pissed off! Plus you won’t tell me what you mean about Jack.”

”Jack will be fine, Cas might be fine, Dean most certainly will not be fine. Let me go and we can talk.”

”Sorry, no deal. Maybe I’ll let you out once I’m sure you’ve told me the full truth... but that’ll probably be a while from now since you haven’t started talking yet.” Sam sounded annoyed.

“This is going nowhere and I’m not changing my mind.” Ruby crossed her arms and turned away.

Ruby was making the 38 year old man feel 25 again, and not in a good way. He hated being reminded of his time with her and now he’s been left to deal with the terrible demon again.

Before Sam could say anything else, Eileen walked back into the room.

She looked down at the girl who was sitting in front of the door. Extremely confused, she started signing. She asked Sam who the girl is and why she’s in their house.

Ruby started talking again before he could respond. “Aww, Sam, is that your wife? You sure she’s good enough for you? You could’ve had me, Sammy.” She pouted dramatically.

Sam ignored her. _She’s just some demon, Cas is in Hell now thanks to her so_ _I’m working on that._

 _Just some demon? Who sent Cas to Hell?_ She signed back with concern. _How did that happen? Can you get him back?_

_Well he’s currently getting Dean back from Hell-_

_Dean is in Hell?!  
  
_

“Sorry to interrupt... well, no I’m not. The girl annoys me.” She chuckled. “Is she pregnant? You’re going to be a horrible father, I could never see you with kids.”

_She doesn’t seem like just some demon, do you know her?_

Ruby had no idea what they were saying. “Hey Sam’s wife, I’m his girlfriend. We go wayyy back. It’s been what, thirteen years? Has he still not told you about me?”

Sam turned back to her. “Shut your mouth!” He yelled before turning back towards Eileen.

_I’m sorry about her. I did know her before, then we killed her, and now she’s back and she won’t leave me alone._

_You’re going to have to explain more than that._

* * *

It had been days. It could’ve even been weeks.

Castiel had entirely lost track of time since he’d been chained up and alone. Every day he had to face more pain. The torture seemed to come out of nowhere. There wasn’t anyone there to do anything to him but it happened anyway.

He still had nothing to do but to think about Dean. His thoughts went from worry, to hope, to anger, and back to worry in an endless cycle.

He knew that time passed differently on earth which meant there was a good chance Sam hadn’t realized he’d been stuck their yet.

The screams continued. “DEAN? JACK? ANYONE?” He shouted until he couldn’t feel his throat.

“DEAN, I’M HERE! I’M GOING TO RESCUE YOU DEAN!”

He couldn’t admit to himself that he needed rescuing. Dean had to be the focus.

Suddenly he started falling. The ground was nowhere in sight.

He started to panic as it became hard to breathe. The sudden realization that he was only human and couldn’t do anything as he fell was terrifying.

Finally, he hit the ground. He still wasn’t prepared for the pain.

Although it felt like his body had shattered he was perfectly fine. Most likely so that something similar could happen all over again.

He refused to let that happen. The determined man stood up, forgetting the pain.

He was no longer tied up, so he could start looking for Dean.

Although Hell seemed huge and dark, he figured it couldn’t be as hard to get through as the Empty.   
  


“DEAN?! I’M HERE!”

* * *

Dean followed the two redheaded girls down the path for a while, holding back his many questions.

They were on their way to seal Heaven apart from Hell, although Dean had no idea how they’d make that happen.

“Are you two sure that this doesn’t feel weird at all?” He asked again.

“Oh come on, Dean. You’re just being paranoid.” Charlie chuckled. “I mean look at us! We’re in Heaven! Stuff can’t go wrong here. Everything is going to be great forever!”

Forever. That hit Dean harder than the truck that wrecked baby.

 _This is nothing like it’s supposed to be!_ Dean thought to himself. _First it was dad and Benny and now this?! This isn’t- this isn’t normal! People aren’t supposed to feel scared here but- I just can’t do this._

He stopped walking, breathing heavily.

“Dean, dear, are you okay?” Rowena asked calmly.   
  


“I-” He tried to figure out what he’d say to avoid lashing out, but there really wasn’t time.

”No! How the hell could I be okay?! This was supposed to be it! I’ve been going and going nonstop for my whole life. This isn’t peace, it was all a lie.” He closed his eyes to avoid the tears which were forming.

”Dean... you’re going to be fine, just breathe.” Charlie put a hand on his shoulder.

”Don’t tell me that I’m gonna be fine!” He yanked himself away from her. “My whole life I pretended to be fine. I did it for Sammy, I did it for Cas, I did it for people like you, but I’ve never been fine! I can’t keep pretending now, I’m still feeling like this and this is what I’m stuck with forever?! There’s never going to be peace and this time there’s no easy way out.”

The former queens of Hell had no idea how to respond. Eventually, Charlie slowly stepped next to Dean again to give him a hug.

He flinched, but accepted the hug. He really needed it. “I’m sorry, I’m so sorry, but I don’t know what to do anymore.”

Charlie kept hugging him. “Listen to me Dean, you never have to be sorry for telling us how you feel. Yeah, I also think it’s weird that you’re this anxious in Heaven but we’re gonna figure it out. Until we do, just know we’re here for you.”

Dean couldn’t stop hugging her yet as he was still hiding his tears. “I was never ready for forever. I just wanted to rest.”

* * *

  
Castiel was determined. He hadn’t been able to find anyone yet, but since he was making his way through Hell that was probably a good thing.

Although it would be perfect to just find Dean and leave, he knew he had to prepare for more.

There would most likely need to be another demon deal.

Dean wouldn’t like that of course, but Cas knew it might be the only option. He was prepared to stay there forever if it meant getting Dean out.

He was starting to feel like he had been walking for days with no progress.

“Dean- Dean I’m- I’m here-” His voice was slipping away after all of the yelling.

Just as he was losing hope yet again, he started seeing something different. As he got closer, he realized it was fire. There were huge flames that seemed to form a path to a cage.

This cage was nothing like Lucifers cage. While the outside seemed similar, he couldn’t see into it at all. It was like there were walls inside.

The fire spiraled up the sides of the cage. There was so much heat coming from it that Cas couldn’t go any closer.

”DEAN?!” His voice cracked.

 _He has to be in there. He’s probably being tortured, I can’t imagine what he’s going through. I have to get in there right now._ He thought.

He walked as close as he could towards the massive flames. As he looked around, Cas noticed there didn’t seem to be a way in.

“No! I have to get in there! Please, someone help!”

Still in pain from the fall, he collapsed onto the ground in defeat. “If anyone is here, please help me. I’ll take anyone!”

“Anyone, you say?” A voice called out from behind him.

“You- how are you here?!”

“Oh relax, Feathers. Yeah, yeah, the Empty woke me up and spit me out just like you and god knows who else.”

“Crowley-” Cas stood up and turned to face him.

“Yes, of course it’s me. Now I heard you desperately need absolutely anyone so you’ve got me, what do you want?” Crowley crossed his arms.

“We need to save Dean.”

* * *

Charlie held Rowena’s hand as she kept her other arm around Dean. They continued walking in silence.

Charlie kept opening her mouth as if about to speak, but she couldn’t find the right thing to say.

Dean was so far off in thought that he payed no attention to where they were going. He trusted Charlie and Rowena... for the most part, so he allowed himself to spiral through his thoughts.

“What if we can’t do it? What if everything is going wrong because Heaven and Hell have been connected for too long and we can’t separate them? What if we get sucked into hell at the last second and are stuck there forever?” Dean was thinking out loud.

“Since when have you been this concerned about things before they happen? It’ll be okay, I do know what I’m doing.” Rowena said with a sigh.

“Well I’m sorry that this is really weird to me. I mean everything was going- okay... and suddenly I’m here and you’re here and I feel like I know nothing again!” He paused before adding, “And why the hell isn’t Cas here yet?! He’s supposed to be here!”

“Hold up, Castiel is dead too?” Charlie asked.

“Of course he’s dead too! The stupid son of a bitch left me and he said it was to save me. I would’ve died with him. I would’ve let the whole world fall apart for him. But instead he left me without giving me a chance to say anything!” He kicked a rock across the ground. “He said he loved me and then he left me, and now he hasn’t been here to see me at all.”

“Whoa, wait, what? Like, he loves you loves you? Or like ‘Hey bro, I love you man, but I swear it’s not gay at all’” Charlie said in a very bad Dean impression.

Dean rolled his eyes. “He really loves me. There was a stupid deal with the empty and something about true happiness, and he just went on and on about me and what he can’t have... I couldn’t say anything back because the whole time I thought it would take him away from me, but I didn’t have to say anything anyway. He was gone and I- I didn’t get to say anything. He died thinking I didn’t love him too.”

“So... you do love him?” Charlie asked.

“I hate him! I hate him so much for doing that to me! I hate that he thought he couldn’t have me. Most of all, I hate that I love him so much and he doesn’t know it. I need to tell him!” Dean felt so weird about saying it out loud, but after years of repressing all of his feelings, it felt so good.

”Well great, we’re gonna find him as soon as we get this done.” Charlie promised.

”That’ll be soon, because we’re here.” Rowena said as she pointed ahead.

It looked like the front of a translucent cage that stretched up towards the sky.

“I need to focus so please, don’t distract me.” Rowena looked up at the cage.

“No, stop. How did you get through before? I need to get through first.” Dean said quickly.

“What, why?!” Charlie sounded concerned.

Dean really wasn’t sure why. He knew he might’ve just been paranoid or curious, but he knew he had to get through.

“We can’t let you do that Dean.” Rowena said firmly.

“You have to!” He pleaded.

“No.” Charlie and Rowena both said at the same time.

**Notes for the Chapter:**

> Yeah, every chapter is named after a Mother Mother song and it’s just because I can’t help connecting all of their songs to supernatural so yep-  
> Anyways, sorry I took a bit of a break from writing, but I hope you all like this chapter (or at least get really confused by this chapter and excited for the next one?)


End file.
